Leuprolide

Leuprorelin

Clinical data
Trade names	Lupron, Eligard, others
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a685040
Pregnancy category	X
Routes of administration	implant / injection
ATC code	L02AE02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Biological half-life	3 hours
Excretion	Kidney
Identifiers
IUPAC name N-[1-[[1-[[1-[[1-[[1-[[1-[[5-(diaminomethylideneamino)-1- [2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxo-pentan-2- yl]carbamoyl]-3-methyl-butyl]carbamoyl]-3-methyl- butyl]carbamoyl]-2-(4-hydroxyphenyl)ethyl] carbamoyl]-2-hydroxy-ethyl]carbamoyl]-2-(1H-indol-3- yl)ethyl]carbamoyl]-2-(3H-imidazol-4-yl)ethyl]-5-oxo- pyrrolidine-2-carboxamide
Synonyms	leuprolide (USAN)
CAS Number	53714-56-0 Y
PubChem CID	441410
IUPHAR/BPS	1175
DrugBank	DB00007 Y
ChemSpider	571356 N
UNII	EFY6W0M8TG
KEGG	D08113 Y
ChEMBL	CHEMBL1201199 N
ECHA InfoCard	100.161.466
Chemical and physical data
Formula	C59H84N16O12
Molar mass	1209.4 g/mol
3D model (Jmol)	Interactive image
SMILES CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc3c[nH]c4c3cccc4)NC(=O)[C@H](Cc5c[nH]cn5)NC(=O)[C@@H]6CCC(=O)N6
InChI InChI=1S/C59H84N16O12/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64)/t40-,41-,42-,43+,44-,45-,46-,47-,48-/m0/s1 N Key:GFIJNRVAKGFPGQ-LIJARHBVSA-N N
NY (what is this?)

Leuprorelin, also known as leuprolide, is a manufactured version of a hormone used to treat prostate cancer, breast cancer, endometriosis, uterine fibroids, and early puberty. It is given by injection into a muscle or under the skin.

Common side effects include hot flashes, unstable mood, trouble sleeping, headaches, and pain at the site of injection. Other side effects may include high blood sugar, allergic reactions, and problems with the pituitary gland. Use during pregnancy may harm the baby. Leuprorelin is in the gonadotropin-releasing hormone (GnRH) analogue family of medication. It works by decreasing gonadotropin and therefore decreasing testosterone and estradiol.

Leuprorelin was approved for medical use in the United States in 1985. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. In the United Kingdom a monthly dose costs the NHS about 75.24 pounds. In the United States the equivalent dose has a wholesale cost of 1,011.93 USD. It is sold under the brand name Lupron among others.

Leuprorelin may be used in the treatment of hormone-responsive cancers such as prostate cancer and breast cancer. It may also be used for estrogen-dependent conditions such as endometriosis or uterine fibroids.